In a large dutch oven, heat olive oil over medium high heat. Add the diced apple, onion, carrots and kosher salt. Saute until softened and onions are slightly translucent (do not brown, adjust heat lower if vegetables start to take on color). Add the cinnamon and nutmeg and cook for an additional minute or so until very fragrant.
Add the roasted squash and chicken broth. Heat just to boiling, then reduce heat to low and cover with the lid slightly askew. Simmer for 10 minutes.
Working in batches transfer the mixture to a blender and puree until smooth. If soup is too thick, add additional broth about half a cup at a time. Return the soup to the dutch oven, and add the cream and Calvados. Heat the soup over medium heat, stirring occasionally until it's hot. Taste and adjust seasoning if needed. Serve.